Triphenylphosphine → N-(2-Bromoethyl)-N-[2-(1,1-dimethylethoxy)-2oxoethyl]-L-tryptophan 1,1-dimethylethyl ester

HRID 2185591Notes

Reaction equation

[CH3:1][C:2]([O:5][C:6](=[O:30])[C@H:7]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[N:8]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:10]O)([CH3:4])[CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:57])C(=O)C1>C(Cl)Cl>[CH3:1][C:2]([O:5][C:6](=[O:30])[C@H:7]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[N:8]([CH2:9][CH2:10][Br:57])[CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-N-(2-hydroxyethyl)-L-tryptophan 1,1-dimethyl-ethyl ester (4.64 g; 11.09 mmol) in CH2Cl2 (44 mL; freshly distilled over CaH2) under an inert atmosphere, solid Ph3P (2.9 g; 11.09 mmol) was added. The solution was cooled to 0° C. and then solid NBS (1.97 g; 11.09 mmol) was portionwise added (45 min), waiting for complete dissolution after each addition. The reaction was monitored by TLC:

Workup

additionwas added
waitwaiting for complete dissolution
additionafter each addition

Sources & evidence

ORD record: ord-677bbf329c304a2d8fb6e97c943ad537
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403055B1

Reaction notes

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